I've been thinking of getting a kindle, but many of the textbooks I would love to read on it are not available in native format (they are small textbooks though that would fit on the screen).

However, I happen to have access to a book scanner (or at least something I can feed a book through once I've chopped off the binding). My question is, if I were to scan one of my textbooks and OCR it with Adobe Professional could I then send that PDF to amazon to convert it to the appropriate kindle format? Would this raise flags with them? Is it even legal? How do they know I didn't just download the book illegally? Is there some kind of privacy policy in the book conversion (perhaps they never look at the files that go through their service) so this won't even be an issue?

I'm just trying to figure out if this is an option. There are plenty of books I CAN buy for the kindle but it seems silly for me to have to carry around 5 books that I can't along WITH an ebook reader.

Perhaps there is an alternate procedure for getting something like this done?

I'll let someone else respond to the legalities (and, of course, those vary depending on the country in which you reside, although that is most likely the US if you have a Kindle).

But in actual practice, Amazon won't notice and won't care. Get an SD card and stuff the book there (since you'll run out space eventually otherwise, esp if you add an audiobook or a few podcasts eventually).

Bizarrely, Amazon would probably even convert the PDF to the right format for you, if you wanted (and even wirelessly transfer it for 10 cents).

But, if you are going to do the work of scanning and OCR'ing the book, you might was well just dump it into Word in the first place, then save it as an HTML doc and run it thru mobicreator - this way, you can fix any odd conversion problems and recreate it as needed. You will end up removing any resale value from the book, as well as the ability to keep it for posterity on your bookshelf, but with the way books are changed every semester now, that probably isn't a big deal.

Personally, I'd wait a few months - if the rumored large tablet Kindle comes out and the textbook deals announced all get in place, then you'll be able to download your textbooks instead of buying and spending your study time scanning time.